Development and Application of Dynamic Kinetic Resolution Reaction via chiral pi-allylpalladium complex

2014 Fiscal Year Final Research Report

• Project/Area Number: 24590029
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Musashino University
• Principal Investigator: HIROYA Kou 武蔵野大学, 薬学研究所, 教授 (70192721)
• Co-Investigator(Kenkyū-buntansha): SHIGEHISA Hiroki 武蔵野大学, 薬学研究所, 助教 (60612471)
• Project Period (FY): 2012-04-01 – 2015-03-31
• Keywords: 動的光学分割 / 不斉配位子 / パラジウム錯体 / 不斉全合成 / アルカロイド

Outline of Final Research Achievements

We had found dynamic kinetic resolution reaction, which proceeded via pi-allylpalladium complex including unusual carbon-carbon bond formation reaction. Thus, we have started our research to establish the optimized reaction condition and utilize its product for the enantioselective synthesis of biologically active compounds as our object.
As results, we established the synthetic route of the starting material and clarified a requirement of the substrate to obtain high enantioselectivity. Moreover, we successfully optimized the solvent and reaction temperature, and established to generate chiral Pd(0) complex in situ. Although we also clarified both of chemical yields and enantioselectivity are influenced by the electronic effect of the substituent on the aromatic ring, elusidation of the mechanism for DKR is underway. By the way, we successfully achieved the stereoselective construction of the chiral quaternary carbon center on benzylic position.

Free Research Field

有機合成化学